


Bittersweet nightmare

by Jenchantress_stories



Category: Supernatural
Genre: Bottom Sam Winchester, Forced Masturbation, Forced Orgasm, M/M, Sex Toys, Top Dean Winchester/Bottom Sam Winchester, Wincest - Freeform
Language: English
Status: Completed
Published: 2020-05-24
Updated: 2020-05-24
Packaged: 2021-03-03 02:08:25
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 2
Words: 3,163
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24357067
Author URL: https://archiveofourown.org/users/Jenchantress_stories/pseuds/Jenchantress_stories
Summary: AU for 02x17 - Born Under a Bad SignMeg possessed Sam's body and realised how sweet and beautiful he is. There's not way she is not touching him everywhere, curious what feels good for a male body.In the second chapter, she makes Sam's dream come true against his will, dragging Dean into his nightmare.
Relationships: Dean Winchester/Sam Winchester
Comments: 6
Kudos: 51
Collections: Sam Winchester Prompt-a-thon





	1. Chapter 1

**Author's Note:**

  * In response to a prompt by [Deeranger](https://archiveofourown.org/users/Deeranger/pseuds/Deeranger) in the [SamWinchester_Prompt_a_thon](https://archiveofourown.org/collections/SamWinchester_Prompt_a_thon) collection. 



> **Prompt:**
> 
> So, what if Meg decides she wants to have a little fun with Sam - something that includes way more than just average and good old-fashioned violence?
> 
> \---  
> My first idea was Meg masturbating with Sam's body and then I wanted to drag Dean into this... So, here's my answer to this sweet, dark prompt.

Meg enjoyed the stroll down on Sam's memories. It was all so dark and twisted. The monsters and horrors he has seen, the violence he's been through, the endless neglect by his Dad. The everlasting feeling of being a freak. She sensed something special with this vessel the moment she got inside, a sweet demonic hint.

She enjoyed Sam's body. With a strong body like this, it was a child's play to kill that stupid hunter.   
But playing the puppy-dog-eyes game, talking Dean into shooting him, didn't work. That would have messed Dean up so badly, but they will get there. Maybe their friend Jo can help her out. Meg knew a thing or two to mess with her. Girls in that age are so vulnerable. She would now, she possessed quite a lot. 

Meg checked the mirror. _Look at you, pretty boy. Kinda my taste._ An idea was coming up and she loved it. 

_”Oh, Sam...”_ She sang. _”Wake up, Sammy-boy. Come out and play...”_

Sam came back to his senses, seeing himself in the mirror but quickly realised something's wrong. He can't move. He tried to touch his face but his hands won't listen.  
 _”Sorry, love, but I'm in charge now.”_

Sam panicked and frantically tried to move just a finger, but nothing happens.   
_”Sam, don't be afraid, I'm not going to hurt you.”_  
 _”GET OUT!”_ Sam yelled, but Meg just smiled. 

_”You're a pretty boy, Sammy. I want to look at you.”_

Sam could feel his hands moving, taking of the jacket before working each button of his shirt open, starting from the top. _”I've been inside men before, but only to get them killed... Disgusting bastards.”_ She dropped the first shirt and took off the second, looking at a beautiful male chest in the mirror.

_”But there's something special about you, Sam. I can't put my finger onto it. It's not that psychic thing, there's more...”_ She used his hands to stroke his chest, lightly squeezing his nipples, tracing the line of his muscles.  
Sam felt uncomfortable inside himself but Meg enjoyed each touch. 

_”Oh, I see, in your memories, that girlfriend of yours... Jessica... she loved this. Her lips sucking on your nipples. You immediately had a reaction down here...”_ One hand was on his crotch now, clutching it.   
_”Stop that, please.”_ Sam's voice was small. He had no idea what to do.  
 _”I'm too curious to stop now.”_ She opened the belt, dropping the jeans, discarding them.   
With the fingers on the hem of his underwear, she grinned. _”Let's see how much of a man you really are.”_

With the underwear gone, both hands explored his dick and balls.   
_”Oh, Sam, Jess was a lucky girl. I should have possessed her, at least for a night.”_

She walked Sam to the bathroom where she took some shower gel in his hands, stroking and massaging the limb member between his legs. _”No! NO! Please!”_ He yelled but she didn't care.   
_”Oh fuck, this feels good.”_ She moved his hands, twisting the fingers a little before his dick twitched and grew. Sam tried to fight it but in vain. He was getting hard and aroused against his will.   
_”Oh, Sammy... you are quite a man after all. I'm all honest when I say you are blessed.”_ But Sam felt disgusted seeing it all, his hands were so unfamiliar.   
_”All solid and hard, the complete opposite of a girl's soft, wet pussy. Tell me, how does is feel fucking a girl?”_  
But Sam went silent. 

_”I've been inside so many young ladies and they had memories... so innocent and naïve, thinking they had to do this to become successful, pleasing disgusting over-confident man just to be dropped by the next corner...”_  
There was something like sympathy in her voice, but then Sam remembered what happened to the Meg he and Dean met, how her body was treated and then left to die. 

She laid down on the bed stroking his length, indulging in the arousal.   
_”Sam, don't be a killjoy, talk to me. I'm doing you good, don't you think? Don't you like it.´?”_ But Sam didn't answer.  
 _”Maybe your a different type...”_ His hands travelled further down, right towards his tight entrance. 

_”NO! NO! TAKE YOUR HANDS OF ME!”_ Sam screamed frantically as his fingers started poking.  
 _”Don't say no if you haven't tried.”_

She got up to grab more shower gel. His slick fingers easily gained access, two fingers moving inside of him, exploring.  
 _”STOP! PLEASE! STOP!”_ He yelled, desperately fighting for control. She pushed a third finger in and it hurts. 

She picked up stroking his cock again while fingering his ass. Deep inside, Sam squirmed as he despises his bodies reaction.   
_”This is not bad... very different. Me like.”_ Pulling both hands away, she walked to the bathroom to wash his hands and Sam hoped his nightmare is over.  
 _”Let's see, what else could we push inside your body...”_ Meg looked around and found a beer bottle. With another handful of shower gel, the bottle's neck slipped inside.   
_”GET THAT OUT!”_ But Meg wasn't bothered.   
_”Nah, that's not quite it.”_ She moved the bottle a bit inside him, but pulled out again soon. 

She looked around, but nothing in this motel room felt right for her plan.  
 _”I need to go for a little shopping trip, so you can take a break.”_

Before Sam could say anything, he fell asleep in darkness.

* * *

When Meg pulled Sam back to consciousness, the first thing he spotted right in front of his eyes is a huge plastic phallus.   
_”Hey Sammy, do you think we can get this inside your ass?”_ She grinned and Sam panicked again, thrashing inside. _”GET OUT OF ME! I'LL KILL YOU, I SWEAR!”_   
_”Yeah, you had the chance and you didn't. And the girl died anyway...”_ Meg shrugged. Meg Masters was just another vessel to her. 

_”But I'm not as evil as you think I am. Look at this.”_ She held a bottle of lube up, shaking it a little, before she placed both things onto the bed to undress him. Deep inside, Sam's shivering, waiting for Dean to find him.  
 _If I have to die to stop her, so be it._

_”That's a pretty dark thought, Sam. It's time for some hot stuff.”_ She was generous with the lube as his hands move down again, one working on the limb cock, the other on the tight hole. Sam was mewling - scared and furious about the arousal growing inside of him.   
_”I think we're ready.”_ She held the dildo high, pushing it in his mouth where it barely fits it.   
_”Plastic never tastes good, but still better than some unwashed dick. You boys' hygiene is ridiculous sometimes.”_ She explained while lubing the thing. Up on his knees, she was lowering his body down, the tip pressing hard on his entrance before it gave in, stretching him painfully. He cried out loud in pain as she lowered him further, impaling him inch by inch. 

_”Oh, that's feels really good, don't you think? What's pleasure without a little pain?”_  
 _”Please, take it out...”_ He begged.  
 _”Come on, it's not even half in.”_  
Sam kept groaning uncomfortably, knowing the thing ripped him already.   
_”Stop whining. I had girls who handled worse.”_

The plastic phallus penetrated deeper as one hand started stroking again, milking the first drops of pre-cum out.   
_”Poor, innocent girls going down on old, gross bastards, just to record one song or get a role on a TV show. I've been inside their heads. I know how much it hurts and I can reassure you, that you are fine.”_  
She started bobbing, up and down, thrusting the last inches in.  
 _”I can see you want this, Sammy. I'm holding the evidence in my hand.”_ The cock was firm in his hand, glistening wet from lube.  
 _”No. No, please, stop...”_ Sam tried again.  
 _”You're hard and leaking. I know you'll go off on this. A big, fat cock in your ass turns you on.”_  
Sam just shakes his head, he waits for this to end.  
 _”I know about your thoughts about Dean, how you secretly looked at him showering in that motel with the broken bathroom door. How hard you got...”_  
 _”NO! No...”_ He's shocked she found those memories.  
 _”You can't lie to me, Sammy-boy. I know your dirty little secrets and I love them.”_  
She continued to move, sitting down to take the whole dildo in. Now both hands were stroking the whole length of his dick. The sensation was amazing for Sam's body but his mind was outraged about the violation.

The foreign object stretching him inside felt so repulsive. He was squirming inside but his body didn't stop fucking itself. The climax was building inside him, he heard his own voice moaning in pleasure. Meg ensured he felt it all, every tingle on his skin, inside and outside. She wanted him to go off on his own self-inflicted abuse.

Meg starts bobbing harder, while his fingers clutch tight around his cock, solid meat in his hand. The physical experience felt better with every movement. She let images of Dean crossing his mind, half naked after a shower or on a hot day at a lake. His perfect body, his strong chest. _”I know you jerked off under the shower to these pictures in your head.”_ She moaned out loud, all sensual and aroused while Sam screamed inside, trying to cut himself away but it was useless. 

Meg knew exactly what she was doing, picking all kind of sweet images of his brother from his memories. _”Look at those, how old was Dean there? 16? 17? Weren't you a little too young back then? But already sporting a boner for your brother...”_ More images followed. Dean's mesmerising eyes, the well-shaped ass, him washing his cock thoroughly under the shower. Suddenly Sam felt the jolt of relief when his body came, spilling his load across the bed. 

_”Seriously, it was my first time with a guy and I honestly think I did amazing.”_ His body dropped to the bed with genuine satisfaction.  
 _”Maybe I should try a woman next. Shall we check on your friend Jo?”_ Sam shivered and shook his head, hoping that she will change her mind. Arguing won't help.

As she spread his body over the mattress, the plastic dick slowly slipped out, leaving a sore and burning hole. Sam became silent.

* * *


	2. Bittersweet Nightmare Deluxe

**Summary for the Chapter:**

> Meg makes Sam's dream come true in her own, evil way...

**Notes for the Chapter:**

> Like in the episode, Meg/Sam went to Jo's bar, messing with her mind until Dean came in, saving Jo and attacking Meg/Sam...

Meg didn't expect Dean to throw holy water on her. _He must have figured out something's not quite right. Took him long enough, don't you think?_ She smashed Sam's body through the window and immediately saw a little storage room, perfect for hiding. 

Closing the door behind him, she had another idea.   
_”Okay, Sam, listen. If you don't want anyone to get hurt, you stay right here. Got that?”_ _”Wait, hold on, what...?”_ Before Sam could say anything else, Meg got out of him. Suddenly, he had control over his body, was able to move on his own. But since Meg left without apparent reason Sam had a bad feeling.

He opened the door of the storage room to look outside, but Dean was already standing in front of it.  
 _”Hey, Sam.”_  
 _”Dean!”_ Sam was happy to see him and straightaway wanted to warn him.   
_”Not quite...”_ He said and pushed Sam back into the dark storage room.  
 _”No... no no no no no... Get out of him! Leave my brother alone!”_  
 _”Sam, I'm here to make your dream come true.”_ Dean's voice, but strangely unfamiliar.

Sam stepped back, trying to get further away from the demon possessing his brother, but the storage room wasn't big and he was soon cornered.   
_”Listen closely. Do as I say and Dean won't get hurt. He won't even know or remember, because right now, he's sleeping peacefully inside his own mind. But if you try anything...”_ His voice was playful, but threatening.  
 _”What do you want?”_ Sam was scared and nervous. Having her messing with him was one thing, but now Dean's involved and Sam's more vulnerable than ever.

_”Turn around, drop your jeans and bend over.”_ It was a whisper close to his ear. Sam instantly had tears in his eyes. He doesn't want Dean dragged into this. He was hesitating.   
_”Come on, Sam. Do it now, or Dean will wake up in 3... 2...”_  
 _”NO! No, please...”_ Sam turned his back towards her and did as he's been told, presenting his still sore ass.   
_”Spread those perky cheeks for me.”_ With shivering hands, Sam complied. There was only little light coming from a lantern outside, but it was enough for her to see him. 

The sound of a belt and a fly opening made it hard for Sam to stay calm.   
_”Oh, your brother's blessed too. I regret not checking on your father. Unfortunately for you, I left the lube in our motel room.”_  
Sam was silent, terrified about the horror that is about to happen.

_”Let's see, what turns him on.”_ Meg said while massaging his cock. _”Oh, that's interesting, such a dirty, dirty mind... and that... oh wow... Wouldn't you like to know?”_ Meg was genuinely enjoying the situation.  
 _”Wouldn't you like to know how he thinks about you? How he feels about you? I bet you do.”_   
But instead of giving any further information, she was giggling, sometimes moaning while she prepared Dean.   
During the whole time Sam didn't move, too afraid to piss her off, to endanger Dean. 

_”I think we're ready for the main part.”_ Sam felt his brother's hard cock on his buttocks, then between them, going up and down his rim. He knew Dean had a big one. He knew it would hurt. Saliva was dripping on his tight, pink hole.   
_”Come Sammy, you are far to quiet. I want you to tell me that you want it. I want you to beg for it or I'll just fuck you and Dean will watch.”_  
Sam swallowed hard. _”Please...”_ His voice was thin and shivering.   
_”Please... f...”_  
 _”Please what...?”_  
 _”Please... fuck me. I want you to... to... fuck me...”_

_”Anything for my little brother.”_ He felt the tip of his cock pressing against his entrance, adding more pressure before the head slipped in. Sam groaned in pain.   
_”Oh, that feels good, don't you agree?”_  
 _”Yes...”_

More saliva was dripping on him, trying to ease the penetration but it was not enough. Dean's solid cock got pushed deeper inside and Sam had to fight hard to not pull himself away.   
_”It's not as easy as our toy, I admit, but your hot tight ass around this thick prick is something new... so exciting.”_  
It was agonising being torn apart like this and hearing Dean's voice talking to him. After all, it is his brother's body. The smell, the touch – it was all too familiar. 

Sam could feel every inch of his brother inside of him, penetrating deeper, stretching him wider, filling him up. There was a pain-filled groan slipping from his lips as he eventually felt Dean's pelvis on his.   
_Yes..._ She hissed aroused, the sensation running through Dean's body and the agony of Sam combined felt like a bliss.

Dean's hips started to move and Sam realised that he was holding his breath. It hurt bad but he had to endure it, biting his lower lip to not scream.  
 _”Sam, come on and relax. You dreamed about this. Your pretty Dean pounding your ass. I'm not all evil.”_

He felt Dean's hand going beneath him, grabbing his limb cock.   
_”Oh, what's that? You could do much better a few hours ago.”_ She played with the head of his dick until it twitched.   
_”I knew it. So Sam, I want your hands down there. I want you to take care of the front part and I take care of your back.”_ She bend Dean's body over his, lips close to his ear.  
 _”Make it good and convincing or I'll take a trip with your brother.”_

Sam complied, working on himself with both hands after spitting into them. He had to focus, swallowing the disgust and thinking about something good despite the excruciating pain spreading from his hole to the rest of his body.  
Dean's hands were on his pelvis, holding onto it while Meg used the older one to impale Sam harder. She moaned, she wanted Sam to hear Dean's voice going off on this. _Yes – that's good – I'll fill you up – my sweet little Sammy..._

_”Moan for me, Sammy...”_ But all that came out a shivering groan, Sam hissing his breath, whimpering with every thrust. Meg didn't mind. 

Dean's hand clutched Sam's and helped him stroking this now hard cock.   
_”I'm here for you, little brother.”_ Intensifying the grip on his prick, squeezing it. 

_”You are hard and leaking with your brother's meat inside you, you little sick freak.”_ She placed the hand back to the hips, now violently fucking him, clashing their hips together and Sam cries out loud in pain.   
_”Drop the act, Sam. I know you want this. You fantasized about this under the shower, fucking your soaped hand. You should be kissing my ass for that.”_ Dean's nails were digging in his skin, the fast sound of skin smacking onto skin filling the little storage room mixed with miserably oppressed mewling.   
_”Am I right? Come on you little sick bitch, tell me I'm right.”_   
The intense burning of his hole and the unbearable stretching inside of him left him unable to talk. Sam was squirming beneath, trying not to cry out loud while he was forced to touch himself. 

_”You are one pathetic piece of shit. It was definitely the right choice to make you the cum-hole here.”_ The forceful penetration suddenly stopped and a loud moan was audible. Meg made Dean come and now filling Sam, shooting his load deep inside his body. 

She quickly pulled out and went for Sam's dick one more time, using some swift twists to make him spill too, even though a few drops only.   
_”Well, first time sex is always a little weird, right? Be grateful that Dean doesn't now about your sad performance.”_

Meg sorted Dean's jeans and brought him back to the spot where he picked him up. Alone in the storage room, Sam fell on his knees, letting the tears roll now. His entrance was sore and sticky and he despised it so much. He wanted to throw up but had nothing in his stomach.

It didn't take long and Meg was back inside him, She stood up, pulled his jeans up and wiping away the tears. _”Crying on the floor? You're not so manly after all Sammy.”_ She mocked him while leaving the storage room. His whole body was in pain but she didn't mind.

She pulled out his weapon and smiled with excitement.  
 _”So, here we go. One of you is going to die very soon...”_

Sam crumbled in despair.

**Notes for the Chapter:**

> Thank you so much for reading this! Big hugs! ♥


End file.
